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Asymmetric catalysis of carbon–carbon bond forming reactions using amino acid-derived C1-symmetrical salen ligands

Lookup NU author(s): Professor Michael North, Jamie Hunt

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Abstract

Four amino acids (alanine, valine, phenylalanine and phenylglycine) have been converted into C1-symmetrical salen ligands and complexed to titanium, vanadium, copper and cobalt. The resulting complexes have been used as asymmetric catalysts for asymmetric cyanohydrin synthesis, asymmetric Strecker reactions, asymmetric synthesis of α-methyl amino acids and asymmetric Darzens condensations. Satisfactory levels of asymmetric induction were obtained from reactions in which the (salen)metal complex acts as a chiral Lewis acid, but low levels of asymmetric induction were obtained from reactions carried out under solid-liquid phase transfer conditions. © 2009 Elsevier Science. All rights reserved

Publication metadata

Author(s): Belokon Y, North M, Hunt J

Publication type: Article

Publication status: Published

Journal: Tetrahedron: Assymetry

Year: 2008

Volume: 19

Issue: 24

Pages: 2804-2815

Date deposited: 19/03/2009

ISSN (print): 0957-4166

ISSN (electronic): 1362-511X

Publisher: Elsevier

URL: http://dx.doi.org/10.1016/j.tetasy.2008.11.037

DOI: 10.1016/j.tetasy.2008.11.037

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